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Vacation Rentals in Kailua, HI

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All 103 Rentals in Kailua
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From
$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (9) Make Inquiry
From
$139
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Inquiry
From
$145
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
32 photos Details Reviews (11) Make Inquiry
Also consider
Sharon's Serenity Bed and Breakfast
3 Bedrooms, sleeps 8
$100 - $110 / night
Your Island Home!
3 Bedrooms, sleeps 8
$500 - $995 / night
Peaceful property in lush tropical setting
2 Bedrooms, sleeps 4
$175 / night
Majestic Oceanfront Estate
8 Bedrooms, sleeps 12
$4,990 / night
From
$126
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed July 7, 2014
We enjoyed staying in this neat and clean studio apartment. Sabine and Ray were welcoming and have put a lot of thought into providing everything for guests' comfort. We loved...
4 of 5 stars Reviewed June 28, 2014
We spent 6 nights at Suite Aloha at the end of April. The studio apartment was very clean, nicely furnished and decorated in Hawaiian style. We made use of the large gas barbecue...
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From
$95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 28, 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
3 of 5 stars Reviewed July 6, 2014
Looking for a deal on our Hawaiian getaway, I booked this place after another fell through. I was trying to be thrifty and this looked like it fit our needs. The place is...
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From
$395
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
16 photos Details Reviews (23) Make Inquiry
5 of 5 stars Reviewed April 19, 2014
We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
4 of 5 stars Reviewed November 21, 2013
After 5 weeks travelling in the continental US and Canada with 4 children, we thoroughly enjoyed our week at Kukui House Kailua where we could kick back and relax, enjoy day...
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From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
13 photos Details Reviews (13) Make Inquiry
3 of 5 stars Reviewed July 14, 2014
First of all, the hosts are friendly and helpful. The location of the villa is very convenient to Kailua Beach. There is also a communal washer and dryer which is very handy to...
5 of 5 stars Reviewed January 21, 2014
Quaint beachy atmosphere. Rooms were clean and well cared for. Charming local decor. Sleeps 4 comfortably. The air conditioner worked perfectly. The kitchen was well stocked with...
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From
$449
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 18, 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$175
Per Night
Studio, 1 Bathroom, Sleeps 4
19 photos Details Reviews (34) Make Inquiry
5 of 5 stars Reviewed June 2, 2014
Just left this morning and hated to leave. The place looks just like the photos. It was very clean and spacious. The outdoor lanai was very nice and spacious as well. The...
4 of 5 stars Reviewed March 2, 2013
It was an easy drive from Honolulu Airport with wonderful access to beautiful beach - 3 minutes' walk down the hill to the park. Accomodations were very comfortable (especially...
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From
$185
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
24 photos Details Reviews (2) Make Inquiry
3 of 5 stars Reviewed September 20, 2014
Not pravite pool and hot tub, shared with others lived in that house. No late check out option 11:00 too early. Living room got only fan it's kind hot dining there.
4 of 5 stars Reviewed August 25, 2014
The very best thing about this rental is the beautiful swimming pool! When the fountains are going, it is just like the picture illustrates; very exotic, pretty and relaxing...
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From
$155
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
21 photos Details Make Inquiry
From
$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details Make Inquiry
From
$200
Per Night
Studio, 1 Bathroom, Sleeps 3
16 photos Details Make Inquiry
From
$174
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
13 photos Details Make Inquiry
From
$425
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
18 photos Details Make Inquiry
From
$130
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
18 photos Details Make Inquiry
From
$800
Per Night
8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$330
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
14 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed May 20, 2014
I would highly recommend the Bali House. It had everything that we wanted and needed. It is like staying in your own little resort. The walk to the beach is very easy and...
4 of 5 stars Reviewed April 7, 2014
Bali Hawaii was spacious and nicely appointed. The three of us had plenty of space to spread out and have privacy. What I liked best was the location--a 5 minute walk to the beach...
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From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 28, 2014
This studio is very roomy and comfortable with everything needed for a great stay! We did a lot of site seeing on the island, and it was so refreshing to come back to our studio...
4 of 5 stars Reviewed August 10, 2014
We were 4 people (including a 9y old boy) staying 4 nights in this unit. It is nicely located in a quiet area, clean, and well decorated. There's a flat screen TV (we didn't use...
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From
$285
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
Bookings
26 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed August 25, 2014
Brenda and her co-Horts were so great to work with and very attentive to our needs and request. We had 10 of us and they helped coordinate all the space and rooms we needed to...
5 of 5 stars Reviewed June 11, 2014
We stayed in Palawiki properties with 3-bedroom 2 bath room. The house is spacious , beautiful, lovely and very clean. It is more like a sweet home to my family. The kitchen...
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From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details Make Inquiry
From
$139
Per Night
Studio, 1 Bathroom, Sleeps 3
Booking
8 photos Details Make Inquiry
From
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
15 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 21, 2014
We were a bit apprehensive about being the first renters of this new rental, but took a chance since the location and space seemed ideal. We had a wonderful week staying here...
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From
$179
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
21 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 28, 2014
We enjoyed our time in Kailua. The apartment was perfect. We had a lot of space and everything was very clean.
4 of 5 stars Reviewed April 2, 2014
My husband and I really enjoyed our stay. The location was great. The air condition was not working. The owner tried to correct the problem twice, but could not repair the...
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From
$95
Per Night
Studio, 1 Bathroom, Sleeps 2
10 photos Details Make Inquiry
From
$175
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 22, 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$165
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
30 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 19, 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$450
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
31 photos Details Make Inquiry
From
$935
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
6 photos Details Make Inquiry
From
$550
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Make Inquiry
From
$475
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details Make Inquiry
From
$525
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
27 photos Details Make Inquiry
From
$650
Per Night
6 Bedrooms, 3 Bathrooms, Sleeps 10
21 photos Details Make Inquiry
From
$450
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Make Inquiry
From
$145
Per Night
Studio, 1 Bathroom, Sleeps 3
11 photos Details Make Inquiry
From
$330
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
14 photos Details Make Inquiry
From
$550
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
1 photo Details Make Inquiry
From
$900
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
19 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed April 21, 2014
We just returned from renting this home in Kailua. We were very happy with the home and the owners. The beach was a very short walk and was not crowded at this end. Kailua is a...
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From
$1,250
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed June 18, 2014
Kailua is a quiet community with a small town feel. It has one the largest most beautiful beaches on Oahu. More peaceful and less crowded than Waikiki. Great hosts at...
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From
$139
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details Reviews (21) Make Inquiry
5 of 5 stars Reviewed September 3, 2014
This great little find is located 45 seconds from one of the best beaches in Oahu. It's 5 mins from central Kailua (shops, restaurants, conveniences), and has parking. The place...
5 of 5 stars Reviewed June 2, 2014
Cozy, wonderful studio, best location, just 3 minutes walk from one of the most amazing beaches in the world. Hosts were very helpful and friendly at all times. Looking forward to...
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Book Online(51)
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Suitability

  • Wheelchair access (13)
  • Elder access (35)
  • Suitable for children (41)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (87)
  • Grill (79)
  • Other outdoor space (72)
  • Washer/Dryer (67)
  • Parking (63)
  • View all amenities
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Book Online(51)

Suitability

  • Wheelchair access (13)
  • Elder access (35)
  • Suitable for children (41)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (87)
  • Grill (79)
  • Other outdoor space (72)
  • Washer/Dryer (67)
  • Parking (63)
  • View all amenities
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.